Silicon-containing tributyltin

Trimethyl(trifluoromethyl)silane can be converted into tributyl(trifluoromethyl)tin (40) in quantitative yield by treatment with bis(tributyltin) oxide in tetrahydrofuran under fluoride ion initiation. Tributyl(trifluoromethyl)tin readily trifluoromethylates disilyl sulfides at room temperature giving the corresponding trifluoromethylated di- and trialkylsilancs 41 in high yields. This method provides a new approach for the preparation of silicon-based trifluoro-methylating reagents via transtrifluoromethylation of compounds containing Si — S bonds. 

Summary BusSnH is an effective reagent for partial conversion of Si-Cl into Si-H groups. The hydrogenation mechanism postulates the coordination of the catalyst or the solvent to silicon giving a hypervalent intermediate in the first step, followed by the attack of tributyltin hydride by a single electron transfer or a synchronous hydride transfer. This mechanism implies that the intermediate containing a hypervalent silicon atom reacts faster than the starting tetracoordinate silane. 

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